Insertion Reaction of Benzynes and Stable Sulfur Ylide
- Corresponding author: He Lin, helin@shzu.edu.cn
Citation:
Li Zhijuan, Jian Hui, Wang Weihua, Wang Qiang, He Lin. Insertion Reaction of Benzynes and Stable Sulfur Ylide[J]. Chinese Journal of Organic Chemistry,
;2018, 38(8): 2045-2053.
doi:
10.6023/cjoc201802003
Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 12, 1211.
doi: 10.1246/cl.1983.1211
(a) Shi, F. ; Waldo, J. P. ; Chen, Y. ; Larock, R. C. Org. Lett. 2008, 10, 2409.
(b) Fang, Y. ; Larock, R. C. ; Shi, F. Asian J. Org. Chem. 2014, 3, 55.
(c) Ikawa, T. ; Takagi, A. ; Goto, M. ; Aoyama, Y. ; Ishikawa, Y. ; Itoh, Y. ; Fujii, S. ; Tokiwa, H. ; Akai, S. J. Org. Chem. 2013, 78, 2965.
(d) Swain, S. P. ; Shih, Y. C. ; Tsay, S. C. ; Jacob, J. ; Lin, C. C. ; Hwang, K. C. ; Horng, J. C. ; Hwu, J. R. Angew. Chem., Int. Ed. 2015, 54, 9926.
(e) Mei, G. -J. ; Xu, S. -L. ; Zheng, W. -Q. ; Bian, C. -Y. ; Shi, F. J. Org. Chem. 2018, 83, 1414.
(a) Suh, S. E. ; Chenoweth, D. M. Org. Lett. 2016, 18, 4080.
(b) Bhojgude, S. S. ; Baviskar, D. R. ; Gonnade, R. G. ; Biju, A. T. Org. Lett. 2015, 17, 6270.
(c) Zeng, Y. W. ; Li, G. Y. ; Hu, J. B. Angew. Chem., Int. Ed. 2015, 54, 10773.
(d) Sha, F. ; Huang, X. Angew. Chem., Int. Ed. 2009, 48, 3458.
(e) Yoshida, H. ; Asatsu, Y. ; Mimura, Y. ; Ito, Y. ; Ohshita, J. ; Takaki, K. Angew. Chem., Int. Ed. 2011, 50, 9676.
(a) Xu, D. Y. ; Zhao, Y. L. ; Song, D. P. ; Zhong, Z. L. ; Feng, S. B. ; Xie, X. G. ; Wang, X. L. ; She, X. G. Org. Lett. 2017, 19, 3600.
(b) Dhiman, A. K. ; Kumar, R. ; Sharma, U. J. Org. Chem. 2017, 82, 12307.
(c) Xu, J. K. ; Li, S. J. ; Wang, H. Y. Chem. Commun. 2017, 53, 1708.
(d) Shi, J. ; Qiu, D. ; Wang, J. ; Xu, H. ; Li, Y. J. Am. Chem. Soc. 2015, 137, 5670.
(e) Rao, B. ; Tang, J. ; Wei, Y. ; Zeng, X. Chem. -Asian J. 2016, 11, 991.
(f) Sundalam, S. K. ; Nilova, A. ; Seidl, T. L. ; Stuart, D. R. Angew. Chem., Int. Ed. 2016, 55, 8431.
(g) Tao, Y. ; Zhang, F. ; Tang, C. Y. ; Wu, X. Y. ; Sha, F. Asian J. Org. Chem. 2014, 3, 1292.
(h) Rao, B. ; Tang, J. H. ; Zeng, X. M. Org. Lett. 2016, 18, 1678.
Zhang, B. X.; Kang, Y. Q.; Shi, R. X. Chin. J. Org. Chem. 2016, 36, 1814(in Chinese).
Fraústo daSilva, J. R.; Williams, R. J. P. The Biological Chemistry of the Elements, Oxford University Press, New York, 2001.
Li, X. J.; Sun, Y.; Huang, X.; Zhang, L.; Kong, L. C.; Peng, B. Org. Lett. 2017, 19, 838.
doi: 10.1021/acs.orglett.6b03840
Li, H. Y.; Xing, L. J.; Lou, M. M.; Wang, H.; Liu, R. H.; Wang, B. Org. Lett. 2015, 17, 1098.
doi: 10.1021/ol5036326
Li, Y. Y.; Qiu, D.-C.; Gu, R. R.; Wang, J. L.; Shi, J. R.; Li, Y. J. Am. Chem. Soc. 2016, 138, 10814.
doi: 10.1021/jacs.6b06981
Liu, F. L.; Chen, J. R.; Zou, Y. Q.; Wei, Q.; Xiao, W. J. Org. Lett. 2014, 16, 3768.
doi: 10.1021/ol501638x
Matsuzawa, T.; Uchida, K.; Yoshida, S.; Hosoya, T. Org. Lett. 2017, 19, 5521.
doi: 10.1021/acs.orglett.7b02599
(a) Cong, Z. S. ; Li, Y. G. ; Du, G. F. ; Gu, C. Z. ; Dai, B. ; He, L. Chem. Commun. 2017, 53, 13129.
(b) He, L. ; Guo, H. ; Li, Y. Z. ; Du, G. F. ; Dai, B. Chem. Commun. 2014, 50, 3719.
(c) Cong, Z. S. ; Li, Y. G. ; Chen, L. ; Xing, F. ; Du, G. F. ; Gu, C. Z. ; He, L. Org. Biomol. Chem. 2017, 15, 3863.
(d) Li, Y. Z. ; Wang, Y. ; Du, G. F. ; Zhang, H. Y. ; Yang, H. L. ; He, L. Asian J. Org. Chem. 2015, 4, 327.
(a) He, L. ; Pian, J. X. ; Shi, J. F. ; Du, G. F. ; Dai, B. Tetrahedron 2014, 70, 2400.
(b) Pian, J. X. ; He, L. ; Du, G. F. ; Guo, H. ; Dai, B. J. Org. Chem. 2014, 79, 5820.
(c) Liu, K. ; Liu, L. L. ; Gu, C. Z. ; Dai, B. ; He, L. RSC Adv. 2016, 6, 33606.
(d) Liu, L. L. ; Li, Z. J. ; Gu, C. Z. ; He, L. ; Dai, B. J. Saudi Chem. Soc. 2017, 21, 458.
(e) He, L. ; Pian, J. X. ; Zhang, J. ; Li, Y. Z. Chin. Chem. Lett. 2012, 23, 1359.
(f) Zhang, J. ; Liu, K. ; Jian, H. ; Li, Z. J. ; He, L. Tetrahedron Lett. 2017, 58, 2964.
(g) Jian, H. ; Liu, K. ; Wang, W. H. ; Li, Z. J. ; Dai, B. ; He, L. Tetrahedron Lett. 2017, 58, 1137.
(h) Li, Z. J. ; Wang, W. H. ; Jian, H. ; Li, W. J. ; Dai, B. ; He, L. Chin. Chem. Lett. 2018, DOI: 10.1016/j.cclet.2018.04.003.
Ahire, M. M.; Thoke, M. B.; Mhaske, S. B. Org. Lett., 2018, 20, 848.
doi: 10.1021/acs.orglett.7b04003
Aggarwal, V. K.; Grange, E. Chem.-Eur. J. 2006, 12, 568.
doi: 10.1002/(ISSN)1521-3765
Insu, K.; Chulbom, L. Angew. Chem., Int. Ed. 2013, 52, 10023.
doi: 10.1002/anie.201303669
Wang, Y. H.; Cai, W.; Liu, Q.; Meng, Q. H.; Cheng, Y. B.; Yang, T.; Zhang, G. F.; Xiang, J. N.; Wu, C. D. WO 2013029338, 2013.
Toni, M.; Morgane, G.; Ruben, M. Angew. Chem., Int. Ed. 2016, 55, 5053.
doi: 10.1002/anie.v55.16
Insu, K.; Chulbom, L. Angew. Chem., Int. Ed. 2013, 52, 1.
doi: 10.1002/anie.201209858
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
Yang Lei , Jieqiong Cai , Daming Sun , Caihong Tao . Exploration and Practice of Integrating Moral Education with Engineering Talent Development in the Instruction of “Principles of Chemical Engineering”. University Chemistry, 2025, 40(3): 230-236. doi: 10.12461/PKU.DXHX202406071
Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . 优化氮化碳纳米片/球形共轭聚合物S型异质结界面电场以促进析氢反应. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-. doi: 10.1016/j.actphy.2025.100095
Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
Huakang Zong , Xinyue Li , Yanlin Zhang , Faxun Wang , Xingxing Yu , Guotao Duan , Yuanyuan Luo . Pt/Ti3C2 electrode material used for H2S sensor with low detection limit and high stability. Chinese Chemical Letters, 2025, 36(5): 110195-. doi: 10.1016/j.cclet.2024.110195
Shahua Huang , Xiaoming Guo , Lin Lin , Guangping Chang , Sheng Han , Zuxin Zhou . Application of “Integration of Industry and Education” in Engineering Chemistry: Improvement of the Pesticide Fipronil Production. University Chemistry, 2024, 39(3): 199-204. doi: 10.3866/PKU.DXHX202309064
Jingyu Cai , Xiaoyu Miao , Yulai Zhao , Longqiang Xiao . Exploratory Teaching Experiment Design of FeOOH-RGO Aerogel for Photocatalytic Benzene to Phenol. University Chemistry, 2024, 39(4): 169-177. doi: 10.3866/PKU.DXHX202311028
Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095